Configurational stability of chlorophosphines

Inorganic Chemistry

Volumn 42, Issue 2, 2003, Pages 420-427

  Humbel, Stéphane ^a,b   Bertrand, Cyrille ^a   Darcel, Christophe ^d   Bauduin, Christophe ^c   Jugé, Sylvain ^a,d  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

^c UNIVERSITÉ DE CERGY PONTOISE   (France)

^d UNIVERSITÉ DE BOURGOGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE DERIVATIVE; CHLOROPHOSPHINE; HALOGEN; HYDROBROMIC ACID; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CATALYSIS; CHIRALITY; CONFORMATION; DENSITY; EVALUATION AND FOLLOW UP; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 0037467773     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic026128u     Document Type: Article

References (64)

1. (a) Brunner. H.; Zettlmeier. W. Handbook of Enantioselective Catalysis with Trapsition Metal Compounds, Products and Catalysis, Vol. 1; VCH: Basel, Switzerland, 1993.
2. (b) Ojima, I. Catalytic Asymmetric Synthesis; VCH: New York, 1993.
3. (c) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. (d) Palmer, M. J.; Wills, M. Tetrahedron: Asymmetry 1999, 10, 2045-2061.
5. (e) Tenaglia, A.; Heumann, A. Angew. Chem., Int. Ed. 1999, 38, 2180-2184.
6. Brunner, H.; Zettlmeier, W. Handbook of Enantioselective Catalysis with Transition Metal Compounds, Ligands-References, Vol. 2: VCH: Basel, Switzerland, 1993.
7. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
8. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
9. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
10. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
11. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
12. For recent, selected examples of enantioselective catalysis using diphosphine ligands, see: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1999, 121, 4545-4554. (b) Burk, M. J.; Bienewald, F.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290-3298. (c) Blaser, H. U.; Buser, H. P.; Jalett, H. P.; Pugin, B.; Spindler, F. Synlett 1999, 867-868. (d) Zhang, Z.; Zhu, G.; Jiang, Q.; Xiao, D.; Zhang, X. J. Org. Chem. 1999. 64, 1774-1775. (e) Fehr, M. J., Consiglio, G.; Scalone, M.; Schmidt, R. J. Org. Chem. 1999, 64, 5768-5776. (f) Kuwano, R.; Ito, Y. J. Org. Chem. 1999, 64, 1232-1237.
13. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
14. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
15. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
16. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
17. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
18. For recent, selected enantioselective catalysis using diphosphinite or diphosphite ligands, see: (a) Clyne, D. S.; Mermet-Bouvier, Y. C.; Nomura, N.; Rajanbabu, T. V. J. Org. Chem. 1999, 64, 7601-7611. (b) Hu, W.; Yan, M.; Lau, C. P.; Yang, S. M.; Chan, A. S. C.; Jiang, Y.; Mi, A. Tetrahedron Lett. 1999, 40, 973-976. (c) Chen, Y.; Li, X.; Tong, S. K.; Choi, M. C. K.; Chan, A. S. C. Tetrahedron Lett. 1999, 40, 957-960. (d) Kündig, E. P.; Saudan, C. M.; Bemardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220- 1223. (e) Reetz, M. T.; Mehler, G. Angew. Chem. Int. Ed. 2000, 39, 3889-3890. (f) Diéguez, M.; Pàmies, O.; Ruiz, A.; Castillon, S.; Claver, C. Chem. Eur. J. 2001, 7, 3086-3094.
19. (a) Agbossou, F.; Carpentier, J. F.; Hapiot, F.; Suisse, I.; Mortreux, A. Coord. Chem. Rev. 1998, 178-180, 1615-1645.
20. (b) Devocelle, M.; Mortreux, A.; Agbossou, F.; Dormoy, J. R. Tetrahedron Lett. 1999, 40, 4551-4554.
21. For a recent review on chelating monophosphines or derivative ligands, see: Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48 (3), 315-324.
22. For selected examples of the synthesis of phosphorus ligands using chlorophosphine as an electrophilic block, see: (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (b) Deaton, D. N. In Encyclopedia of Reagents for Organic Synthesis, Vol. 2; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995. (c) See also refs 4 and 5.
23. For selected examples of the synthesis of phosphorus ligands using chlorophosphine as an electrophilic block, see: (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (b) Deaton, D. N. In Encyclopedia of Reagents for Organic Synthesis, Vol. 2; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995. (c) See also refs 4 and 5.
24. For selected examples of the synthesis of phosphorus ligands using chlorophosphine as an electrophilic block, see: (a) Sprinz, J.; Helmchen, G. Tetrahedron Lett. 1993, 34, 1769-1772. (b) Deaton, D. N. In Encyclopedia of Reagents for Organic Synthesis, Vol. 2; Paquette, L. A., Ed.; Wiley: Chichester, U.K., 1995. (c) See also refs 4 and 5.
25. For a typical synthesis of phosphorus ligands using chlorophosphine as the phosphide source, see: Peer, M.; de Jong J. C.; Kiefer, M.; Langer, T.; Rieck, H.; Schell, H.; Sennhenn, P.; Sprinz, J.; Steinhagen, H.; Wiese, B.; Helmchen, G. Tetrahedron 1996, 52, 7547-7583.
26. (a) Rauk, A.; Allen, L. C.; Mislow, K. Angew. Chem. Int. Ed. Engl. 1970, 9, 400-414.
27. (b) Baechler, R. D.; Mislow, K. J. Am. Chem. Soc. 1971, 93, 773-774.
28. (a) For molecular orbital (MO) arguments, see: Levin, C. C. J. Am. Chem. Soc. 1975, 97, 5649-5655.
29. (b) For valence bond (VB) arguments, see: Bent, H. A. Chem. Rev. 1961, 61, 275-311.
30. Omelanczuk, J. J. Chem. Soc., Chem. Commun. 1992, 1718-1719.
31. The kinetic resolution of tert-butylchlorophenylphosphine (1d) has been described for the preparation of the (thio)phosphoryl derivative with e.e. up to 50% in: Perlikowska, W.; Gouygou, M.; Daran, J. C.; Balavoine, G.; Mikolajczyk, M. Tetrahedron Lett. 2001, 42, 7841-7845.
32. Horner, L.; Jordan, M. Phosphorus Sulfur 1980, 8, 235-242.
33. (a) For a recent high-level computational work on the SN2 reactions of halide ions on neutral halophosphines in the gas phase, see: Sølling, T. I.; Pross, A.; Radom, L. Int. J. Mass Spectrom. 2001, 210/211, 1-11.
34. (b) For corresponding gas-phase measurements: Van Doren, J. M.; DePuy, C. H.; Bierbaum, V. M. J. Phys. Chem. 1989, 93, 1130-1134.
35. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
36. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
37. (b) Becke, A. D. J. Chem. Phys. 1996, 104, 1040-1046.
38. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
39. (d) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
40. (a) Trippett, S. Phosphorus Sulfur 1976, 1, 89-98.
41. (b) Thatcher, G. R. J.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272-2281.
42. (c) Burgada, R.; Setton, R. In The Chemistry of Organophosphorus Compounds, Vol. 3; Hartley, F. R., Ed.; Wiley: New York, 1994.
43. For the concept of biphilicity, which is related to dual electrophilic and nucleophilic properties of the phosphorus center, see: (a) Ivanov, B. E.; Zheltukhin, V. F. Russ. Chem. Rev. 1970, 39, 358-372. (b) Smith, D. J. H. In Comprehensive Organic Synthesis. Vol. 2; Sutherland, I. O., Ed.; Pergamon Press: Oxford, U.K., 1979; pp 1121-1187.
44. For the concept of biphilicity, which is related to dual electrophilic and nucleophilic properties of the phosphorus center, see: (a) Ivanov, B. E.; Zheltukhin, V. F. Russ. Chem. Rev. 1970, 39, 358-372. (b) Smith, D. J. H. In Comprehensive Organic Synthesis. Vol. 2; Sutherland, I. O., Ed.; Pergamon Press: Oxford, U.K., 1979; pp 1121-1187.
45. More details on this minor aspect of the mechanism are provided in the Supporting Information.
46. - that does not occur in toluene.
47. The foremost preparation of 7b by reaction of an excess of HBr with 1b has been described by: Dörken. C. Chem. Ber. 1888, 21, 1506-1515.
48. (a) Jugé, S.; Stephan, M.; Achi, S.; Genêt, J. P. Phosphorus Sulfur 1990. 49/50, 267-270.
49. (b) U.S. Patent 5 043 465, 1989.
50. (c) Jugé, S.; Stephan, M.; Laffitte, J. A.; Genêt, J. P. Tetrahedron Lett. 1990, 31, 6357-6360.
51. (d) Jugé, S.; Stephan, M.; Genêt, J. P.; Halut-Desportes, S.; Jeannin, S. Acta Crystallogr. 1990, C46, 1869-1872.
52. (e) Jugé, S.; Stephan, M.; Merdès, R.; Genêt, J. P.; Halut-Desportes, S. J. Chem. Soc., Chem. Commun. 1993, 531-533.
53. (f) Kaloun, E. B.; Merdès, R.; Genêt, J. P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455-463.
54. (g) Moulin, D.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 1999, 10, 4729-4743.
55. (h) Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939-3956.
56. (i) Uziel, J.; Darcel, C.; Bauduin, C.; Moulin, D.; Jugé, S. Tetrahedron: Asymmetry 2001, 12, 1441-1449.
57. Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem. Soc. 1985, 107, 5301-5303.
58. Brodie, N.; Jugé, S. Inorg. Chem. 1998, 37, 2438-2442.
59. (a) Chodkiewicz, W.; Jore, D.; Wodzki, W. Tetrahedron Lett. 1979, 20, 1069-1072.
60. (b) Mikolajzyk, M. Pure Appl. Chem. 1980, 52, 959-972.
61. (c) Nielsen, J.; Dahl, O. J. Chem. Soc., Perkin Trans. 2 1984, 553-558.
62. (d) Kolodiazhnyl, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332.
63. Lindner, E.; Dieter Merkle, D. Hiller, W.; Fawzi, R. Chem. Ber. 1986, 119, 659-668.
64. Du Mont, W.-W.; Schumann, H. J. Organomet. Chem. 1977, 128, 99-114.